Holley Chesser
Holley Chesser is a technology and customer experience leader whose career began in education. She spent the early years of her professional journey as a classroom teacher, where she naturally gravitated toward using technology and data to inform instruction and improve student outcomes. Her ability to translate complex tools into practical classroom application led to opportunities to train other teachers, first within her school and later at the county level, helping educators integrate technology into everyday instruction. This foundation in teaching and enablement eventually transitioned into her first corporate role with Scantron, where she trained adult learners on education technology and software adoption.
From there, Holley expanded into large-scale software implementation and customer growth roles across the United States, primarily in business-to-government and SaaS environments. At Scantron and later organizations including Wonderschool, Brightwheel, and PeopleBench, she focused on driving adoption, improving retention, and building systems that supported long-term customer success. Her work consistently centered on lifecycle engagement, conversion from free to paid users, and designing data-informed strategies that improved both customer outcomes and revenue performance. Over time, she built a reputation for connecting cross-functional teams and creating operational clarity in complex, multi-stakeholder environments.
Today, Holley serves at Moultrie, an e-commerce and subscription-based company focused on wildlife trail cameras and digital products, where she is leading a transformation toward a customer-centric operating model. She is building the company’s first comprehensive customer intelligence foundation, including Snowflake-based data infrastructure, a customer data platform, and a lifecycle engagement system powered by Braze. Her work focuses on unifying customer data, defining meaningful behavioral signals, and turning insights into targeted, multi-channel engagement that improves retention, conversion, and customer lifetime value. Across her career, she has remained focused on one core theme: using data, systems, and strategy to create better, more sustainable customer experiences.
• University of Alabama at Birmingham
Master of Arts - MA, Early Childhood Education/Developmental Psychology
• The University of Alabama
Bachelor of Arts - BA, Counseling Psychology
What’s the best career advice you’ve ever received?
The best advice I've ever received came from my dad, and it's really simple but powerful. He taught me as a child that you can look at a glass full of water and see it as half full or half empty, and how you perceive that is how you approach any kind of obstacle in life. If you approach things as always the glass is half full, it doesn't mean it's going to be easier for you to get through, but your perspective is going to really impact how you get through that scenario or that challenge that may come up. I think that's one of the best things I've really taken with me throughout every kind of scenario - perspective is everything. It allows you to be resilient in a way that really is your mindset becoming resilient. You're always going to be faced with things, and if you can approach challenges that way, that's what helps you get through it. It's something I even say to my kids now.
What advice would you give to young women entering your industry?
If I could go back and tell my younger self, it's this: don't wait until you feel ready, because you're never going to feel ready. Step into things before you have all the answers and trust that you'll figure it out. You're taking that leap of faith for a reason, and trusting in yourself really goes a long way. Stop waiting for permission to be perfect or for perfection. Most of my growth in my career has come from stepping into things that felt a little bit bigger than me at the time. Use your voice early, don't sit back. Ask questions, share your perspective - that's how you really grow and that's how people really start to see you as a leader. I work with mostly men, so I know this is important.
What are the biggest challenges or opportunities in your field right now?
Right now, the biggest challenge and opportunity is really coming in and laying the foundation and establishing that baseline. The real challenge comes once we have this baseline in place and we can really understand our customers better - it's figuring out how we're going to optimize that and push from the baseline to those optimal metrics we're trying to achieve, whether it's retention, customer lifetime value, or other key metrics. Generally speaking, a lot of companies see customer experience as just a call center, so the challenge is proving with data that CX and my team really directly impact revenue, conversion, and retention. We're constantly answering questions like, what does this campaign actually drive? Is it worth the investment? The fragmented customer data usually lives everywhere, and we're the first that's really coming in and putting that all together. I think the real challenge is trying to balance that long-term system build versus providing short-term results, and then scaling that without breaking operations. It's really trying to scaffold that approach with what we're trying to do.
What values are most important to you in your work and personal life?
In both my personal and work life, I always try to operate with authenticity. I think taking ownership and accountability is really important, and I try to showcase authentic impact over just activity and being busy. I really care about what moves the needle, not just being busy. Building, creating clarity, and simplicity is also really key for me - I value making complex things easy to understand and execute. With the data piece, I focus on turning data, systems, and strategy into clear plans that teams can follow, and I kind of carry that over at home too. I value ownership, impact, and clarity, and I'm driven by building things that actually matter, whether that's at work or personal. I care a lot about creating meaningful experiences that allow for continuous growth, both personally and professionally.